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Glycol Ethers


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Glycol Ethers

  1. 1. GLYCOL ETHERS • long-term shelf-life of products • work at low concentrations Glycol ethers, with both an ether and • a lack of residual odour alcohol functional group in the same • good biodegradability molecule, are one of the most versatile • Improve the wetting properties of classes of organic solvents from which water- based products liquid substances derived. They are both hydrophilic (soluble in water) and Glycol Ether products are produced lipophilic (soluble in oils). As they are through continuous processes of excellent co-solvents, they enable non- selectively reacting an alcohol and miscible substances to be mixed with each ethylene oxide. other. Glycol ethers are characterized by their excellent solvency, chemical stability and The chemical structure of long compatibility with water and a number of hydrocarbon chain resist to solubility in organic solvents. The dual functionality water, while ether or alcohol groups present in the EGBE and DEGBE solvents introduce the promoted hydrophilic accounts for their unique solvency solubility performance. This surfactant-like properties. As a class of products, EGBE structure provides the compatibility and DEGBE solvents are: between water and a number of organic solvents, and the ability to couple unlike • Mild-odored solvents for many resins, phases. oils, waxes, fats and dyestuffs Because of these specific properties, they • Coupling agents for many water/organic are included in the composition of many systems products for use by industry or the general public. • Miscible with a wide range of polar and non-polar organic solvents The main properties of glycol ethers are that they are soluble in water and in oils. • Miscible with water in most cases These properties make them very useful for numerous applications for industry and A coupling agent is defined as a compound the general public. Indeed glycol ethers which provides a chemical bond between very often play a crucial role in the two dissimilar materials, usually an formulation of products that would not inorganic and an organic. function without them. Some of them make it possible to use water for dissolving This strong solvency leads to the selection substances that would otherwise remain of certain EGBE and DEGBE solvents for insoluble. This means that their use, in low formulations of cleaners. concentrations, has avoided the need to resort to other solvents that may present • Solvents for grease and grime in risks to safety (inflammability) and/or for industrial cleaning and specialty the environment (evaporation of volatile formulations organic compounds). • Coupling solvents for hard-surface Glycol ethers also have other cleaners and other soap-hydrocarbon characteristics: systems • long-term stability of formulations 1
  2. 2. All international research and evaluations EGBE is an organic solvent with the show that glycol ethers do not accumulate formula C6H14O2. It is a colorless liquid, in the environment, because they break ether-like odour. It is a butyl ether down in the air within a few hours by of ethylene glycol. It is a type of glycol photolysis (= breakdown reaction triggered ether and remains the single most widely by sunlight) and they are biodegradable produced glycol ether. It is primarily used within a few days in the aquatic as a solvent. It evaporates quickly and is environment. completely soluble in water. Glycol Ether products would be classified EGBE is sold commercially under a as “readily”/rapidly biodegradable and variety of names. EGBE is also referred to would not be expected to persist in the by its chemical names: natural environment for a significant period of time. • 2-Butoxy-1-ethanol • Ethylene glycol monobutyl ether Under the right conditions, EGBE and • 2-Butoxyethanol DEGBE can be used for professional • Ethylene glycol butyl ether (EGBE) applications without presenting a risk to • Butyl CELLOSOLVE health. • Butyl glycol ether (BGE) According to Human health classifications for glycol ethers according to the EU dangerous substances directive (67/548/EEC) EGBE Line Structure Glycol Irritant/ Harmful ether corrosive EGBE R36/38 R20/21/ 22 DEGBE R36 N/C EGBE Space-filling Model R20: harmful by inhalation Chemical Name Ethylene Glycol R21: harmful in contact with skin Monobutyl Ether R22: harmful if swallowed CAS Number 111-76-2 R36: irritating to eyes Molecular Formula C6H14O2 R38: irritating to skin Appearance Colorless, liquid Boiling Point 171°C(340°F) at 760 mmHg ETHYLENE GLYCOL BUTYL Structure C4H9-O-CH2-CH2-OH ETHER (EGBE) Solubility Miscible in both water and organic solvents EGBE is a key ingredient in hundreds of products ranging from industrial and consumer cleaning solutions to water- and solvent-based paints and coatings. EGBE’s n-Butanol Ethylene Oxide EGBE popularity stems from several special performance characteristics that also EGBE is produced by reacting ethylene provide economic value. oxide and normal butanol (n-butanol) using a catalyst. If the ratio of ethylene oxide to 2
  3. 3. n-butanol is greater than one, di- and tri- and soaps are miscible with EGBE. ethylene glycol monoethers are produced Accordingly, this product along with the EGBE. is widely employed as a coupling agent to stabilize immiscible ingredients in industrial metal cleaners, in vapor degreasers, in the clarification of oil-water dispersions, and in the formulation of concentrated liquid cleaners. In fabric cleaners, EGBE assists in removing water- soluble stains and aids in brightening the colors of garments. It improves penetrating and wetting action of phosphoric acid-type rust removers. EGBE is used in coatings and cleaner When added to cleaners, EGBE helps lift applications, including many in consumer soil and keeps it suspended until it can be markets. It is used for: rinsed or wiped away. Because EGBE’s chemical structure includes an ether and an • Active solvent for solvent-based alcohol, it can attack water-insoluble oils coatings and greases and water-soluble stains. EGBE thus offers manufacturers a variety • Coalescent for industrial water-based of cleaning capabilities, from heavy-duty coatings industrial jobs to milder janitorial and • Coupling agent for architectural water- household uses. borne coatings • Coupling agent and solvent in EGBE is compatible with both petroleum household and industrial cleaners, rust solvents and water, it is found in a wide- removers, hard surface cleaners and range of coatings – from automotive and disinfectants packaging coatings to wood furniture • Primary solvent in solvent-based silk finishes. It is used widely in water-based screen printing inks industrial paints and coatings. • Coupling agent for resins and dyes in water-based printing inks In household products, EGBE uses include • Solvent for agricultural pesticides glass and tile cleaners, waxes, rust removers and metal polishes. The same EGBE has been used for more than half a properties that allow EGBE to dissolve and century. Today it is used extensively in hold soils and stains in suspension make both water- and solvent-based coatings and the compound an effective ingredient in industrial and consumer cleaners. Cleaners water-based protective paints and coatings. made with EGBE can remove oils, fats, EGBE also acts to dissolve or suspend waxes, greases and baked-on or ground-in pigments and resins until the coating is residues from floors, walls, glass, metal applied to surfaces. Once the coating is parts, and equipment. Paints and coatings applied, EGBE is designed to evaporate, that use EGBE range from lacquers, leaving a uniform, dry finish. varnishes and enamels to water-based coatings and inks. Although some glycol ethers have been EGBE offers superior performance in shown to cause adverse reproductive many hard-surface cleaners and related effects and birth defects in laboratory Cleaning formulations. Mineral oils, water animals, EGBE does not show the same 3
  4. 4. pattern of toxicity as these other glycol DIETHYLENE GLYCOL BUTYL ethers. Human experience and animal ETHER (DEGBE) studies have shown that EGBE is unlikely to cause adverse health effects when DEGBE is a clear, liquid with a mild ether products are used as directed. Still, when odor. It is a solvent with an extremely low used improperly, EGBE can cause eye, rate of evaporation and is completely water respiratory tract and skin irritation and soluble and serves as a mutual solvent for even burns. soaps, oils and water and as a component of liquid cleaners, “soluble” oils and textile EGBE is unlikely to cause adverse oils. It has found increased use in Cleaning environmental impact because it is not formulations because of its good solvency persistent, does not bioaccumulate (build for greasy soils and waxes. up in the food chain), is readily DEGBE is sold commercially under a biodegradable and has low toxicity to variety of names. DEGBE is also referred aquatic organisms. It moves to water when to by its chemical names: it is released because of its high miscibility, low volatility and minimal • 2-(2-Butoxyethoxy)ethanol tendency to bind to soil or sediment. It • Diethylene glycol monobutyl ether degrades rapidly in water. • Diethylene glycol butyl ether (DGBE) • Butyl CARBITOL™ solvent EGBE is one of the most versatile • Butoxydiglycol chemicals in the marketplace today for a • Diglycol monobutyl ether wide variety of uses. Human experience and animal studies have shown that it is unlikely to cause adverse health effects when used as directed and in accordance with product safety information and good hygiene practices. EGBE studies also show it is unlikely to cause adverse environmental impacts because it is not DEGBE Line Structure persistent, does not bioaccumulate, and has low toxicity to aquatic organisms. Chemical Name Diethylene Glycol Monobutyl Ether Research continues so that industry, CAS Number 112-34-5 government and academic scientists can Molecular Formula C8H18O3 increase our knowledge about EGBE. Appearance clear hydroscopic liquid Boiling Point 231°C at 760 mmHg As with all chemicals, EGBE should be Structure C4H9(OCH2CH2)2OH used with care and in accordance with Solubility Miscible in both water and governmental regulations. EGBE and organic solvents products containing EGBE are not intended to be ingested. Airborne concentrations of EGBE should be n-Butanol Ethylene Oxide DEGBE maintained below permissible exposure limits. Consistent with governmental DEGBE is used as a solvent in coatings standards, skin contact with EGBE before and cleaner applications for industrial and it is diluted in commercial formulations consumer markets. It is also used as a should be avoided. chemical intermediate to produce 4
  5. 5. diethylene glycol monobutyl ether acetate water. Because of these properties, (DBA) and some herbicides, insecticides DEGBE poses a low risk to the and plasticizers. DEGBE is also used in environment. hydraulic brake fluid applications. Specifically, it is used as: • Coupling agent and solvent in household and industrial cleaners, rust removers, hard surface cleaners and disinfectants • Latex coalescent in water-based architectural and industrial coatings • Primary solvent in solvent-based silk screen printing inks • Coupling solvent for resins and dyes in water-based printing inks • Solvent for ball point and felt tip pen inks, and textile dyeing and printing • Coalescent for latex adhesives • Deactivator and stabilizer for agricultural pesticides • Diluent in hydraulic brake fluid applications DEGBE is practically non-toxic to aquatic organisms on an acute basis. It is readily biodegradable and does not bioaccumulate (build up in the food chain). DEGBE moves to water when it is released because of its high solubility, low volatility and high soil mobility. It degrades rapidly in 5